The present invention relates to new optically active terpene hydroxysulfonic acids and hydroxysulfonate salts.
Preparation of sulfonic acid salts from a sulfite, a bisulfite, or a thiosulfate and an alkylene or cycloalkylene oxide is known. Such preparation can be found in Culvenor et al., J. Chem. Soc., 278 (1949), Lauer & Hill, J. Org. Chem., 58, 1873 (1936), and Lambert & Ross, J. Chem. Soc., 46 (1949). It should be noted that in the foregoing citations, no useful products of the sulfonate salts have been proposed therein. The reaction of .alpha.- and .beta.-carene oxides with sodium sulfite has been reported by E. Myslinski and E. Michalett, Rocz. Chem., 41, 285-289 (1973) and 47, 1755-1758 (1973), to give hydroxysulfonate salts.
The optically active terpene hydroxysulfonic acids of this invention are prime candidates for resolving agents and their hydroxysulfonate salts are useful as surfactants, for example. Advantages in the process for their preparation include the preservation of the optical purity of the feed epoxide in the product sulfonate salt, and the substantial absence of racemization and isomerization products from the process.